Triazine derivatives of piperidinylamidines

Abstract

A compound of formula (I) ##STR1## in which R 1 and R 2 are e.g. hydrogen or methyl, R 3 is e.g. a group ##STR2## or a group R 5 X-- with R 5 being e.g. hydrogen, C 1 -C 18 -alkyl or C 3 -C 18 -alkenyl and X being e.g. --O--, --S-- or ##STR3## and R 6 is as defined for R 5 , or R 3 represents a 5-membered to 7-membered nitrogen containing heterocyclic group with the free valency on the nitrogen, n is an integer from 2 to 6, and R 4 is a nitrogen containing organic radical of a valency equal to n. The compounds of formula (I) are particularly effective in stabilizing organic material against oxidative, thermal and/or light induced degradation.

We claim: 
     
       1. A compound of formula (I) ##STR86## in which R 1  is hydrogen, O.sup.·, CN, NO, cyanomethyl, C 1  -C 12  -alkyl, C 3  -C 12  -alkenyl or C 3  -C 12  -alkynyl, with the proviso that the carbon atom attached to the nitrogen atom is a primary carbon atom, C 7  -C 12  -aralkyl, C 1  -C 12  -acyl, 2,3-epoxypropyl, 2,3-dihyroxypropyl or OH-monosubstituted C 2  -C 6  -alkyl, R 2  is hydrogen, C 1  -C 18  -alkyl, C 5  -C 18  -cycloalkyl, C 6  -C 18  -aryl or C 7  -C 18  -aralkyl, R 3  is a group ##STR87## in which R 1  and R 2  are as defined above, or R 3  is a group R 5  X-- in which R 5  is hydrogen, C 1  -C 18  -alkyl, C 2  -C 6  -alkyl which is monosubstituted by OH, by C 1  -C 18  -alkoxy or by C 2  -C 18  -dialkylamino, C 5  -C 18  -cycloalkyl, C 3  -C 18  -alkenyl, C 6  -C 18  -aryl, C 7  -C 18  -aralkyl or a group of the formula (II) ##STR88## in which R 1  is as defined above, and X is --O--, --S-- or ##STR89## with R 6  being as defined for R 5 , or R 3  is a 5-membered to 7-membered nitrogen containing heterocyclic group with the free valency on the nitrogen selected from the group consisting of 1-pyrrolidinyl, piperidino, morpholino, 1-hexahydroazepinyl and 4-methyl-1-piperazinyl, and n is an integer from 2 to 6, if n is 2, R 4  is a group ##STR90## in which p is zero or 1, R 7  and R 9 , which are identical or different, are as defined for R 5 , and R 8  is a direct bond, C 2  -C 18  -alkylene, C 5  -C 18  -cycloalkylene, C 6  -C 18  -arylene, C 7  -C 18  -aralkylene or C 4  -C 14  -alkylene which is interrupted in the chain by one or two oxygen atoms or by one or two ##STR91## groups, in which R 10  is hydrogen, C 1  -C 12  -alkyl, C 6  -C 12  -cycloalkyl or a group of the formula (II), or R 4  is the divalent radical of a 5-membered to 7-membered heterocyclic compound with two nitrogen atoms and the free valencies on the nitrogen atoms selected from the group consisting of ##STR92## or R 4  is ##STR93## in which R 11  is as defined for R 10 , q is an integer from 2 to 6 and r is zero or 1, if n is 3, R 4  is ##STR94## in which R 12 , R 15 , R 16 , R 18 , R 20 , R 22 , R 23  and R 25 , which are identical or different, are as defined for R 10 , and R 13  and R 14 , which are identical or different, are C 2  -C 12  -alkylene or C 4  -C 14  -alkylene which is interrupted in the chain by an ##STR95## group, R 17 , R 19 , R 21  and R 24 , which are identical or different, are C 2  -C 12  -alkylene and s is zero or 1, if n is 4, 5 or 6, R 4  is a group ##STR96## in which R 26  and R 29 , which are identical or different, are as defined for R 10 , and R 27  and R 28 , which are identical or different, are C 2  -C 12  -alkylene and t is 1, 2 or 3, or, if n is 4, R 4  is additionally a group ##STR97## in which R 30  is as defined for R 10 , R 31  and R 32 , which are identical or different, are C 2  -C 12  -alkylene and R 33  is as defined for R 3 , or, if n is 6, R 4  is additionally a group ##STR98## in which R 30 , R 31  and R 32  are as defined above. 
     
     
       2. The compound according to claim 1, wherein R 1  is hydrogen, methyl, allyl, benzyl or acetyl, R 2  is hydrogen, C 1  -C 12  -alkyl, C 6  -C 9  -cycloalkyl or C 6  -C 9  -alkyl, R 3  is a group ##STR99## in which R 1  and R 2  are as defined above, a group R 5  X-- with R 5  being hydrogen, C 1  -C 8  -alkyl, C 6  -C 9  -cycloalkyl, allyl or a group of the formula (II) and X being --O-- or ##STR100## where R 6  is hydrogen, C 1  -C 8  -alkyl, C 6  -C 9  -cycloalkyl, allyl or a group of the formula (II), or R 3  is 1-pyrrolidinyl, piperidino, morpholino or 1-hexahydroazepinyl and n is an integer from 2 to 6, and, if n is 2, R 4  is a group ##STR101## in which R 7  and R 9 , which are identical or different, are hydrogen, C 1  -C 12  -alkyl, C 6  -C 9  -cycloalkyl, allyl or a group of the formula (II) and R 8  is C 2  -C 6  -alkylene, C 6  -C 15  -cycloalkylene, phenylene, xylylene or C 4  -C 12  -alkylene which is interrupted in the chain by one or two oxygen atoms or by one or two ##STR102## groups, or R 4  is ##STR103## if n is 3, R 4  is ##STR104## in which R 12 , R 15 , R 16 , R 18  and R 20 , which are identical or different, are hydrogen, C 1  -C 12  -alkyl, C 6  -C 9  -cycloalkyl or a group of the formula (II), R 13  and R 14 , which are identical or different, are C 2  -C 6  -alkylene or C 4  -C 6  -alkylene which is interrupted in the chain by an ##STR105## group, R 17  and R 19 , which are identical or different, are C 2  -C 6  -alkylene and s is zero or 1, if n is 4, 5 or 6, R 4  is a group ##STR106## in which R 26  and R 29 , which are identical or different, are hydrogen, C 1  -C 12  -alkyl, C 6  -C 9  -cycloalkyl or a group of the formula (II), R 27  and R 28 , which are identical or different, are C 2  -C 6  -alkylene and t is 1, 2 or 3. 
     
     
       3. The compound according to claim 1, wherein R 1  is hydrogen or methyl, R 2  is hydrogen or methyl, R 3  is a group ##STR107## in which R 1  and R 2  are hydrogen or methyl and n is an integer from 2 to 4, and, if n is 2, R 4  is a group ##STR108## in which R 7  and R 9 , which are identical or different, are hydrogen, C 1  -C 4  -alkyl, cyclohexyl, 2,2,6,6-tetramethyl-4-piperidinyl or 1,2,2,6,6-pentamethyl-4-piperidinyl and R 8  is C 2  -C 6  -alkylene, C 6  -C 13  -cycloalkylene or C 4  -C 12  -alkylene which is interrupted in the chain by one or two oxygen atoms or by one or two ##STR109## groups, or R 4  is ##STR110## if n is 3, R 4  is a group ##STR111## in which R 12  and R 15 , which are identical or different, are hydrogen, C 1  -C 4  -alkyl, cyclohexyl, 2,2,6,6-tetramethyl-4-piperidinyl or 1,2,2,6,6-pentamethyl-4-piperidinyl, and R 13  and R 14 , which are identical or different, are C 2  -C 6  -alkylene or C 4  -C 6  -alkylene which is interrupted in the chain by an ##STR112## group, if n is 4, R 4  is a group ##STR113## in which R 26  and R 29 , which are identical or different, are hydrogen, C 1  -C 4  -alkyl, cyclohexyl, 2,2,6,6-tetramethyl-4-piperidinyl or 1,2,2,6,6-pentamethyl-4-piperidinyl, and R 27  and R 28 , which are identical or different, are C 2  -C 6  -alkylene. 
     
     
       4. The compound according to claim 1, wherein R 1  and R 2  are hydrogen, R 3  is a group ##STR114## n is 2, 3 or 4, and if n is 2, R 4  is a group ##STR115## in which R 7  and R 9 , which are identical or different, are hydrogen, methyl or 2,2,6,6-tetramethyl-4-piperidinyl and R 8  is --(CH 2 ) 2-6  --, methylenedicyclohexylene, 4,7-dioxadecane-1,10-diyl or 4,7-diazadecane-1,10-diyl, or R 4  is a group ##STR116## if n is 3, R 4  is a group ##STR117## in which R 13  is a group --(CH 2 ) 2-3  -- and R 14  is a group --(CH 2 ) 2-3  -- or 3-azahexane-1,6-diyl, and, if n is 4, R 4  is a group ##STR118## 
     
     
       5. The compound according to claim 1, wherein R 1  and R 2 , which are identical or different, are hydrogen or methyl, R 3  is a group ##STR119## in which R 1  and R 2  are as defined above or R 3  is a group R 5  X-- in which R 5  is C 1  -C 8  -alkyl, C 2  -C 6  -alkyl which is monosubstituted by C 1  -C 6  -alkoxy or is allyl and X is ##STR120## with R 6  being hydrogen or C 1  -C 8  -alkyl or R 3  is morpholino, and n is an integer from 2 to 4, and, if n is 2, R 4  is a group ##STR121## in which R 7  and R 9 , which are identical or different, are hydrogen, C 1  -C 4  -alkyl or 2,2,6,6-tetramethyl-4-piperidinyl, R 8  is methylenedicyclohexylene, C 2  -C 6  -alkylene or C 4  -C 12  -alkylene which is interrupted in the chain by one or two oxygen atoms or by one or two ##STR122## or R 4  is a group ##STR123## if n is 3, R 4  is ##STR124## in which R 12  and R 15  are hydrogen and R 13  and R 14 , which are identical or different, are C 2  -C 6  -alkylene or C 4  -C 6  -alkylene which is interrupted in the chain by one ##STR125## group, and, if n is 4, R 4  is ##STR126## in which R 26  and R 29  are hydrogen and R 27  and R 28 , which are identical or different, are C 2  -C 6  -alkylene. 
     
     
       6. The compound N,N'-bis-[2,4-bis-[N",N"'-bis-(2,2,6,6-tetramethyl-4-piperidinyl)-formamidino]-1,3,5-triazin-6-yl]-1,6-hexanediamine, N,N'-bis-[2,4-bis-[N",N"'-bis-(2,2,6,6-tetramethyl-4-piperidinyl)-formamidino]-1,3,5-triazin-6-yl]-4,4'-methylene-bis-(cyclohexylamine), N,N'-bis-[2,4-bis-[N",N"'-bis-(2,2,6,6-tetramethyl-4-piperidinyl)-formamidino]-1,3,5-triazin-6-yl]-N-methyl-1,3-propanediamine, N,N'-bis-[2,4-bis-[N",N"'-bis-(2,2,6,6-tetramethyl-4-piperidinyl)-formamidino]-1,3,5-triazin-6-yl]-4,7-dioxadecane-1,10-diamine, N,N',N"-tris-[2,4-bis-[N"',N IV  -bis-(2,2,6,6-tetramethyl-4-piperidinyl)-formamidino]-1,3,5-triazin-6-yl]-3-azapentane-1,5-diamine or N,N',N",N"'-tetrakis-[2,4-bis-[N IV ,N V  -bis-(2,2,6,6-tetramethyl-4-piperidinyl)-formamidino]-1,3,5-triazin-6-yl]-4,7-diazadecane-1,10-diamine according to claim 1. 
     
     
       7. The compound according to claim 1, wherein n is 2, 3 or 4. 
     
     
       8. The compound according to claim 1, wherein R 1  and R 2  are independently hydrogen or methyl. 
     
     
       9. The compound according to claim 1, wherein R 3  is a group ##STR127##